It was a smart move on all sides when the New York Yankees decided to extend Gerrit Cole’s contract by four seasons on November 4. The Yankees will now have their ace back, and Cole will remain in the Bronx.

The Yankees will have other needs in that area, even though Cole’s return to the rotation was the first step toward making this rotation great in 2025. Luckily for them, right-hander Jack Flaherty is one of several starts available.

In 2024, Flaherty brought his career back to life by helping the Los Angeles Dodgers in the final stretch and during the postseason. Given the possibility of a $100 million deal, he may have increased his stock more than any other pitcher on the market.

The most recent to imply that he would was MLB Trade Rumors’ Darragh McDonald. McDonald said that he expected Flaherty to sign a five-year, $115 million contract with the Yankees during MLB free agency.

In terms of “prove-it” deals, Flaherty is among the most prosperous cases in recent history. After a stellar 2019 season, shoulder problems wrecked the former first-round choice and top prospect, who went from being one of the National League’s emerging young aces to an injury reclamation in a matter of years.

In 18 outstanding starts with Detroit, Flaherty recorded a 2.95 ERA, 32% strikeout rate, and 4.6% walk rate. Although he wasn’t quite as effective with Los Angeles, he still pitched 55 1/3 innings with a 3.58 ERA ball to the Dodgers, striking 26.1% of his opponents while walking 8.1% of them, McDonald reported on November 4. “The season-long numbers held up well overall, and Flaherty will now be the youngest of the top end starters available when he returns to the open market at age 29, but without a qualifying offer because he is not eligible to receive one after being traded midseason.”

During the Trade Deadline, the Yankees showed interest in Flaherty.

It wouldn’t be shocking if the New York Yankees expressed interest in Flaherty this winter.

They were reportedly interested in acquiring him prior to the trade deadline, but he was ultimately moved to the Los Angeles Dodgers.

The New York Post’s Jon Heyman claims that the Yankees were concerned about Flaherty’s alleged lower back ailment.

Heyman tweeted on October 24 that the Yankees were considering a possible trade with the Tigers for Flaherty but had backed out due to a rumored lower back issue. Since the Yankees were the only playoff club with additional starters and weren’t rotationally weak, the opposing call didn’t affect them too much. The Tigers reportedly pursued Will Warren, a highly sought-after right-hander.

Despite the discussions that have taken place since the trade deadline, Yankees general manager Brian Cashman informed reporters that they were unable to reach an agreement for him.

According to ESPN’s Jorge Castillo, Cashman stated, “If I could have matched up, I would have brought Jack Flaherty in at the end of the day, and I had difficulty matching up.” “And I don’t have him because of that.”

How the Yankees Would Benefit from Flaherty

The postseason showed the New York Yankees rotation why it could be improved. In crucial situations, pitching wins games, and maybe things would have turned out differently if they had Flaherty.

After struggling before this season with a 4.84 ERA between 2022 and 2023, the right-hander had some worries, but this year’s performance was unforgettable.

With 162.0 innings pitched and 194 strikeouts, Flaherty appears to be returning to his former form. A team like the Yankees might want to sign him to a long-term contract because of his outstanding strikeout performance.

The Cardinals’ $80 million star shipped to the Yankees in an exciting blockbuster.

This winter, the St. Louis Cardinals will focus on finding ways to reduce payroll while giving young players opportunities in the majors. As a result, several popular players may likely leave the roster, either through trades or by not receiving contract extensions. Among those rumored to be potential trade assets is a beloved Cardinals bullpen member, who could interest the New York Yankees.

“Teams in search of a closer should look to the National League Central, where two of the league’s best will be available,” ESPN’s Jeff Passan noted on Monday regarding winter trade speculation.

This season, Ryan Helsley pitched 66 1/3 innings for St. Louis, finishing with a 7-4 record, a 2.04 ERA, a 79-to-23 strikeout-to-walk ratio, a .210 batting average against, a 1.10 WHIP, and a league-leading 49 saves.

“Potential suitors for a closer include the New York Yankees, Los Angeles Dodgers, Boston Red Sox, Texas Rangers, and San Francisco Giants, though realistically, any team would welcome adding Williams or Helsley to its bullpen,” noted Jeff Passan.

Spotrac estimates Helsley’s market value at nearly $80 million over a six-year contract, or about $13 million annually, following his outstanding 2024 season with the Cardinals.

The Cardinals’ greatest chance to replenish their underperforming farm system this offseason will probably be to trade the flamethrower.

It takes time and frequently involves making difficult choices to rebuild a franchise. Regretfully, the Cardinals may need to trade Helsley in order to advance. It might be advantageous for St. Louis’ future to send him to a big-market team like the Yankees.